12 Romantic Restaurants in the Heart of Chicago

Looking for a great date night restaurant in downtown Chicago? Check out this list of 12 romantic restaurants in Chicago, from the eyes of a local, and you’re sure to find something you love.

After seven years living in the heart of downtown Chicago, my husband and I spent many a night out on the town. Having kids put a but of a damper on our “restauranting” but we definitely hit up quite a few date night restaurants before our little ones locked us down a bit. 🙂

In the spirit of Valentine’s Day, let me share with you a host of my favorite spots to grab a romantic bite to eat in the heart of the city (pun intended, get it? Heart?).

Dinner En Blanc ~ This annual, invite only dinner will totally woo you. I haven’t been yet, but my friends have told me about it, and it sounds so cool. After registering for the event (if you make the cut), you dress in elegant all white and arrive at a location that’s a mystery to everyone until the day of the dinner. You bring your own table and chairs, and it’s the chicest picnic in town. (They actually hold the event in various cities all over the world. )

Signature Room ~ A bit cliche, but the views from the top of the Hancock Tower are stunning. If possible, request a table by the window overlooking Lake Michigan. You’ll be glad you played the squeaky wheel a bit to get the “best seat in the house” oil. Just before we moved to Chicago, we visited for a weekend to find an apartment (knowing the job transfer was in the works). It happened to be the weekend of our first anniversary, and the staff kindly served us a fancy dessert plate with “Happy Anniversary” written in chocolate sauce, which I readily ate.

La Madia ~ This local wine and artisan pizza gem may not be your traditional dark and sensual romantic restaurant. But the food is great, you can get plenty of wine, and they have a small wine room that you might be able to request if you play your cards right.

RPM Steak ~ Defining a steakhouse as romantic might be in the eye of the beholder. I always love a good steak dinner, though, and this is one of the best, so it’s on my list of top date night dinners for me.

Sapori Trattoria ~ Something about Italian always seems to speak romance. This little Italian restaurant in a northern neighborhood of the city has a great little menu and good food. It’s a bit off the beaten path for a traditional tourist, but I think finding local gems makes a vacation so much sweeter.

Geja’s Cafe ~ Chocolate anyone? At this fondue restaurant, be sure to save space for dessert. After all, isn’t the chocolate fondue really the reason you go out to a restaurant like this? They also have many dark, private booths and tables, so you’ll definitely feel the romantic vibe.

Osteria Via Stato ~ Another Italian restaurant, this one resides smack dab in the middle of the tourist area. Surprisingly, given it’s location, it attracts more local clientele than one might initially imagine. This is a total favorite of ours that we’ve been to WAY too often.

Zed451 ~ Just call it the best darn brunch you ever did have. It’s a little expensive. It’s worth every penny. Arrive hungry!

Piccolo Sogno ~ Back to life, back to Italian. While impressive in the winter, this wonderful restaurant will blow your socks off during the summer. They have an enormous private and quiet patio behind the restaurant that takes you right out of the middle of the city while only being a mile or two from the Willis Tower. Good food. Great outdoor vibe. Perfect summer dinner date.

Mindy’s Hot Chocolate ~ The food is good. The dessert? Amazing! It probably goes without being said that you shouldn’t leave without ordering a hot chocolate. You’ll need to grab a cab or jump on the Blue Line to get to this restaurant, presuming you’re coming from “tourist central” where I lived and I believe you still currently reside.

Sunda & Mercadito ~ These two restaurants aren’t exactly ‘romantic’ but they’re awesome for a swanky date, so I wanted to add them. They also are Asian and Mexican restaurants, respectively, which helps round out the diversity of the selections I’ve included.

If you’re in the Chicago area, be sure to check out one of these restaurants. They won’t disappoint!

Hi! I'm Jen, editor of Honestly Modern. Welcome to this space all about Sustainable Living for Modern Families. Dive in for ideas to help families pursue more eco-conscious and intentional living in a modern world. Find out more about Why Modern Matters!

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